Dyes derived from benzo[a]phenoxazine – synthesis, spectroscopic properties, and potential application as sensors for l-cysteine / Aleksandra Grzelkowska in COLORATION TECHNOLOGY, Vol. 133, N° 2 (04/2017)  

[article]  inCOLORATION TECHNOLOGY > Vol. 133, N° 2 (04/2017) . - p. 145-157 Titre : Dyes derived from benzo[a]phenoxazine – synthesis, spectroscopic properties, and potential application as sensors for l-cysteine Type de document : texte imprimé Auteurs : Aleksandra Grzelkowska, Auteur ; Jolanta Kolinska, Auteur ; Malgorzata Zaklos‐Szyda, Auteur ; Radoslaw Michalski, Auteur ; Jolanta Sokolowska, Auteur Année de publication : 2017 Article en page(s) : p. 145-157 Note générale : Bibliogr. Langues : Anglais (eng) Catégories : Chromatographie en phase liquide à hautes performances Colorants -- Synthèse Etude in vitro Photochimie Spectrométrie de masse Thiols Toxicologie cellulaire Index. décimale : 667.2 Colorants et pigments Résumé : Several benzo[a]phenoxazine dyes containing a maleimide moiety have been synthesised and characterised by proton nuclear magnetic resonance spectroscopy and mass spectrometry. The spectroscopic properties, such as absorption and emission spectra, of these dyes – 9-maleimido-5H-benzo[a]phenoxazin-5-one (7a), 6-chloro-9-maleimido-5H-benzo[a]phenoxazin-5-one (7b), and 6-bromo-9-maleimido-5H-benzo[a]phenoxazin-5-one (7c) – were examined. These compounds were evaluated as potential fluorescent and colorimetric probes for the detection of biothiols. Results show that the studied compounds exhibit colorimetric and fluorescent responses to l-cysteine at pH 7.4. In the presence of l-cysteine, the fluorescence intensity of synthesised dyes is greatly enhanced. The addition of l-cysteine to solutions of dyes 7a to 7c also results in red shifts of their absorption bands. The cytotoxic effect of tested dyes 7a to 7c against human neuroblastoma cells (SH-SY5Y) was determined by MTT assay. The fluorescent response of these compounds to thiols SH-SY5Y was examined. The results show that the tested compounds exhibit fluorescent response in this cell line, and the benzo[a]phenoxazine dyes substituted in the 6-position with a halogen (7b and 7c) are less toxic against cells under experimental conditions than their unsubstituted analogue (7a). Note de contenu : - EXPERIMENTAL : General - Synthesis - Photochemical experiments - Studies of the spectroscopic response of the dyes to thiols - UPLC/MS - Determination of cell viability and studies of the response to thiols in living cells - RESULTS AND DISCUSSION : Synthesis and spectroscopic studies - Studies of the spectroscopic response to thiols - UPLC and mass spectral analyses of products formed in the reaction with L-Cys - Cell viability and response to thiols in vitro DOI : 10.1111/cote.12261 En ligne : https://drive.google.com/file/d/15o-TDla3f6bzE6z4zT7QuFvXlTiic_rz/view?usp=drive [...] Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=28228 [article]

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Synthesis and application of dyes derived from benz[cd]indol-2(1H)-one as visible-light-absorbing polymerisation photoinitiators / Rafal Strzelczyk in COLORATION TECHNOLOGY, Vol. 132, N° 4 (08/2016)  

[article]  inCOLORATION TECHNOLOGY > Vol. 132, N° 4 (08/2016) . - p. 320-326 Titre : Synthesis and application of dyes derived from benz[cd]indol-2(1H)-one as visible-light-absorbing polymerisation photoinitiators Type de document : texte imprimé Auteurs : Rafal Strzelczyk, Auteur ; Radoslaw Michalski, Auteur ; Radoslaw Podsiadly, Auteur Année de publication : 2016 Article en page(s) : p. 320-326 Note générale : Bibliogr. Langues : Anglais (eng) Catégories : Colorants -- Synthèse Lumière -- Absorption Photoamorceurs (chimie) Photochimie Polyaddition Index. décimale : 667.3 Teinture et impression des tissus Résumé : Several potential initiators based on benz[cd]indol-2(1H)-one dye have been synthesised and evaluated in the radical polymerisation of a system containing trimethylolpropane triacrylate under visible light. Absorption, fluorescence, and phosphorescence spectra and the electrochemical properties of these novel dyes were determined. Owing to the presence of an appropriate hydrogen donor group in their structure, these photoinitiators do not need an extra coinitiator to initiate the polymerisation process. During photopolymerisation they act both as a triplet sensitiser and as a hydrogen donor. The relationship between the polymerisation rate and the triplet-excited-state reduction potential suggests that initiating radicals are formed from the triplet state via hydrogen transfer. This mechanism is supported by density functional theory calculations. 8-Bromo-6-[(2-sulphanylethyl)sulphanyl]benzo[cd]indol-2(1H)-one and 8-bromo-6-sulphanylbenz[cd]indol-2(1H)-one may be applied as visible-light initiators of free radical polymerisation to obtain a low-molecular-weight polymer. Note de contenu : - General - Synthesis - Photochemical experiments - Quantum chemical calculations DOI : 10.1111/cote.12218 En ligne : https://onlinelibrary.wiley.com/doi/epdf/10.1111/cote.12218 Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=26734 [article]

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